Taking the Leap: Stories From Women Who Have

Many women I know talk about reinventing their careers. They hate their jobs, or are just bored, but can’t seem to break free of the shackles of a secure paycheck, health insurance and whatever other benefits they’ve come to comfortably rely on. Yet others, somehow muster the courage to make big changes in their careers for the sake of sanity, family, job satisfaction — and in many cases, a great paycheck.

Much has been documented about why more women don’t take the leap. The hard-wiring of female brains can cause us to focus too much on past failures, or dream up future failures based on past experiences. Emotional memory runs long and deep in female brains. All of this impacts confidence and the willingness to take future leaps.

As proof that many women do take the leap and never look back, I offer up these examples as documented in my new book, Money On The Table, How To Increase Profits Through Gender-Balanced Leadership. These are a few of the stories I collected from successful women entrepreneurs that should give us all encouragement and confidence to act on our intuition and our dreams.

Kathy Cabello, president and CEO of Cabello Associates, Inc., made the decision to leave what she considered a great job opportunity to start her own strategic marketing company many years ago. “I worked for a great company, and they did provide me with flexibility,” she said. But when the company asked her to relocate, she decided she would strike out on her own. “I had two young daughters and my husband had just started a business. It would have been very difficult to uproot our lives.” While she initially worked more hours to get her business up and running and didn’t take a salary, the return on that investment was the ability to manage her own schedule and prioritize her family when she needed to, without the guilt or difficulty of managing others’ expectations. “When my daughter forgot her flute, or I needed to go to a parent-teacher conference or some other event,” she added, “it was much easier to rearrange my own schedule versus one that was made for me.”

Jen Petro, owner of DropLeaf Communications, is another example of a talented professional female who decided to start her own business for the sake of flexibility. Flexibility to Petro didn’t just mean flexibility with her time but also the flexibility to do the work she enjoyed most. “I had some great jobs and worked with some great people, many who were mentors to me,” she noted. “But when you have a job, you don’t get to pick and choose what you work on. I wore many hats and had to do it all. Now, I can take the work I enjoy and I’m good at and either decline or delegate work that’s not a good fit for me.”

Petro is also the mother of three children, and her work-family schedule is better aligned. “After we started our family, I really wanted autonomy and the ability to manage my own schedule,” she said. While she has been approached many times over the years to take a job for one of her clients, she’s not interested. “I can’t imagine ever going back,” she added, referring to an environment that won’t be able to provide the choices in work and the ability to manage her own time

Many women who don’t have children are also driven to strike out on their own for many of the same reasons. Women particularly want to have personally rewarding careers doing work they are interested in, which often results in the drive to work more not less, but on their own terms.

Nicole Webre, CEO and founder of Livewell Properties, a real estate development company in New Orleans, and also president of Webre Consulting, put her law education and experience in zoning and city planning to use when she started her first company in 2013. “I was unhappy because I did not feel in control of my life and finally realized I had skills and expertise that people would pay for outside of working for an organization.” Webre says she works many more hours since owning her own business, but it’s because she’s energized by her work.

Based on my interviews, I believe more women would like to take the leap to start their own businesses and profit from their skills, in order to have more control over their lives, but the lack of confidence and willingness to take risks gets in their way. Webre confirms this point: “Not having the responsibility of providing for a large family gave me some financial flexibility, but I still had to build the confidence that my business would work and take the financial risk to get started. I withdrew a big chunk of my savings to pay the bills while I worked on getting my business off the ground. Within one day after I officially opened, I had three clients. People were incredibly responsive, and it was not because they were doing me any favors. They needed and wanted my expertise. I encourage my friends in similar circumstances to take the risk, but the fear of failure keeps them from doing it.”

The bottom line is that you can make a change and have a second career if you really want it. The women I know who have been successful in doing so created thoughtful plans for their transitions rather than simply acting on whims. They set goals, created business plans and enlisted the help and advice of others who had done the same. Careful planning increased their confidence. Did they experience some bumps along the way? Sure. But bumps happen everywhere, even in stable, profitable companies. It’s not a question of whether you’ll experience challenges or not, just how you will navigate through them.

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